Photographer: Eliana Aponte/Bloomberg

Cuba’s the Hot New Destination, if You Can Satisfy All the Rules

Navigating U.S. and Cuba regulations before you fly is no picnic on the beach.

It’s best to clear up one thing first, if you’re a U.S. citizen: Cuba is not the new Aruba or Montego Bay.

Congress has prohibited American tourists from visiting what John F. Kennedy once called “that imprisoned island” since 1960, and the resumption of commercial air service won’t soon change that. A Cuba trip requires that your reason for travel aligns with one of a dozen permitted categories of activities that the U.S. Treasury Department has outlined as part of the gradual easing of travel restrictions.

Hurdles or not, plenty of Americans are likely to hop a plane to see an island that’s been verboten for decades, mixing wanderlust with the allure of the unknown. But before U.S. travelers can start cursing spotty Cuban Wi-Fi, they’ll need to run a modest regulatory gauntlet, from satisfying the proper travel category to obtaining visas and health insurance, plus sorting out whether a U.S. bank-issued credit card or debit card even works there.

The first obstacle is determining how a trip fits into the permissible reasons for visiting Cuba. No men in black suits and sunglasses will grill you at the gate about why you’re going—or why you went—and airlines aren’t legally on the hook for fibbers flying south to hit the beach or stroll Havana’s sunny Malecón. But make no mistake: The category you choose when booking a ticket isn’t just a checked box, it’s a legal affidavit. Clicking one of them willy-nilly isn’t wise because the U.S. government requires airlines to retain them for five years.

Each airline will probably handle the online booking process in a slightly different manner. American Airlines Group Inc., for example, presents all 12 categories on its site and requires that a customer’s trip fit one before proceeding. JetBlue Airways Corp. will make ticket buyers select a specific category.

“We don’t want to be in the position of telling customers what category they qualify for, so yes, there is going to be some onus placed on the traveler to determine which one of these [Treasury] categories they apply for,” said Jakob VanLeeuwen, an international planning analyst for JetBlue, which announced on Thursday that it has scheduled its first Cuba flight for Aug. 31.

JetBlue's booking screen for Cuba itineraries.
JetBlue's booking screen for Cuba itineraries.
JetBlue Airways

After that, there's health insurance to sort out because Cuba mandates that foreign travelers be covered. JetBlue plans to bundle an insurance policy, from Asistur, a Havana-based insurer, into its tickets to address the government requirement. (The $3 per day premium covers accidents and injuries.) Other airlines are still working through ways to streamline the logistics. American, for example, has contracted with a Cuba Travel Services, a Los Angeles-area charter operator, to help arrange visas for customers. The company will call each passenger booked for Cuba to help sort through visa rules and other requirements. 

“When people go to an airline’s website and they say, ‘Here are the categories and I have to select one, what does that mean,’ they’re going to have questions,” said Michael Zuccato, general manager of Cuba Travel Services, which is making the transition from being a Cuba tour operator to a service provider. The company’s goal is to render a trip to Cuba as simple as one to any other destination by the time a passenger shows up at the airport, he said.

Both American and JetBlue also plan to acquire Cuban “tourist” visas to sell at their U.S. gateway airports for those who aren’t traveling for business, journalism, or other reasons that require a specific Cuban visa. Airport-sold visa prices haven’t been announced, although JetBlue says it won’t add a profit or service fee.

Of the 10 airlines that have been granted routes from the U.S., American is the largest. Soon after JetBlue’s inaugural flight next month, it announced, its first flight from Miami to Cienfuegos will take place on Sept. 7. A smaller carrier, Florida-based Silver Airways Corp., will begin service from Fort Lauderdale, Fla., a week before. The rest are still making plans.

For the 20 daily flights allowed to Havana, airline requests for routes exceeded the supply by a 3-1 margin. Several carriers and airports, including JetBlue, Silver, and Denver, objected to the tentative grants made last week. Replies to the objections are due on Friday, and the U.S. Department of Transportation could issue the final awards soon after. At that point, the carriers will be ready to announce their schedules and fares. They have 90 days to start the new service.

The vast majority of the U.S. airline business to Cuba is expected to be “VFR travel,” or those visiting friends and relatives, with most of the traffic originating in Florida. That’s where most of the Cuban diaspora in America has settled, and it's the state that collected the bulk of the recent DOT routes.

Those looking to fly to Cuba may want to follow the lead of their seafaring brethren. Fathom, the Carnival Corp. brand that began cruises there in May, advises travelers who organize their own people-to-people exchange programs to retain records of their activities, per Treasury guidelines. Specifically, Fathom tells customers to document their time on the island with “a combination of receipts, travel journal, itinerary” and to keep the documentation for five years. The cruise line has no insight into whether U.S. officials audit this information, spokeswoman Jody Venturoni said. Better safe than sorry.

The same guidelines apply to air travelers, although carriers aren’t likely to be as explicit with the advice. Nor are widespread audits expected of Cuba travelers once they return to the U.S., said VanLeeuwen, who led a JetBlue study of its planned Cuba service. “We’ve talked to several firms that specialize in Cuba and pretty much across the board have heard that the enforcement … is highly contingent on the political climate, and more specifically the presidential administration,” he said. Several travelers to Cuba were fined for embargo violations during President George W. Bush’s administration but “under the Obama administration, everyone I’ve talked to said that hasn’t occurred,” VanLeeuwen said. If Republican presidential candidate Donald Trump wins in November, those records may come in handy, whereas a Hillary Clinton administration is unlikely to change course on Cuban foreign policy.

Over time, a jaunt to Cuba will become less onerous in terms of navigating the rules, much as Americans have mastered the intricacies of traveling to China, said Eduardo Marcos, American Airlines’s managing director of alliances and partnerships. “What we’re trying to do here is strike a balance between ensuring all of our customers comply with regulations … and making the customer experience as seamless as possible,” he said. “People are going to get used to it. But it’s going to take months, if not years, to get to that point.”

Before it's here, it's on the Bloomberg Terminal. LEARN MORE